In the Middle Ages, there were markets in several Ryedale villages, Malton, Pickering, Kirkbymoorside, and Helmsley. A monastery was built at Lastingham in 654. Over the centuries, Celts, Romans and Anglo Saxons all inhabited the area around Pickering.[4][5] The district had many ancient Saxon churches and some can still be visited, including St Peter's in Scrayingham, St Martin's in Wharram Percy, St Martins in Bulmer, St Helens in Amotherby, All Saints in Appleton-le-Street, St Peter and St Paul's Church, Pickering, All Saints in Hovingham, Holy Trinity in Stonegrave, St Gregory's Minster, Kirkdale built around 1055-1065, All Saints in Sinnington and St Andrews in Ailsby/Middleton.[6] The Kirkdale sundial above St Gregory's door dates to the 11th century (c. 1055 to 1065),[7]

Ryedale has two impressive castles, both now ruins. The traditional style Pickering Castle was a royal hunting lodge with a moat while Helmsley Castle was a fine medieval structure with double earthworks. The latter was extensively damaged during the Civil War, in 1644. [9]

Once the Malton Bacon Factory was the town's largest employer; Karro Foods now has a processing plant here

The market towns of Helmsley, Kirkbymoorside, Pickering and Malton are the largest centres of population in the Ryedale District with about half of the population living there. The eastern part of the area is dominated by the influence of Scarborough.
Each of the market towns within the Ryedale District has areas set aside for industrial use and small firms engaged in light industry and the service industries occupy these. The largest employer in the district is the pork processor Karro Food Group (once known as The Malton Bacon Factory), now employing around 1,100 people in this location.[12]

In the Scarborough Borough area of the Vale of Pickering a small industrial estate is located at Hunmanby. The main source of employment in the vale is agriculture with tourism and retailing in the market towns and near to the coast.